Simple and effective multi-component one-pot aldol addition/protection reactions of b-ketoesters to a series of aldehydes in the presence Me3SiCl and i-Pr2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.
Multi-component, regio-selective aldol addition of b-ketoesters to aldehydes: scope and applications
DI MOLA, ANTONIA;TEDESCO, Consiglia;PEDUTO, ANTONELLA;DE CAPRARIIS, Paolo;FILOSA, Rosanna;MASSA, Antonio
2011-01-01
Abstract
Simple and effective multi-component one-pot aldol addition/protection reactions of b-ketoesters to a series of aldehydes in the presence Me3SiCl and i-Pr2EtN have been described. The analysis of the scope of the reaction revealed a dramatic dependence of the reactivity on the substrates used. Thus the effect of a catalytic amount of DMF and different reaction conditions was widely investigated. Further transformations of the aldol adducts were particularly useful to give valuable diols and compounds with quaternary stereocenters, while X-ray structural analysis gave also important stereochemical information about this challenging reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
